JPH04133065A - Photoconductive high-polymer compound - Google Patents
Photoconductive high-polymer compoundInfo
- Publication number
- JPH04133065A JPH04133065A JP25472390A JP25472390A JPH04133065A JP H04133065 A JPH04133065 A JP H04133065A JP 25472390 A JP25472390 A JP 25472390A JP 25472390 A JP25472390 A JP 25472390A JP H04133065 A JPH04133065 A JP H04133065A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- toluene
- polymer compound
- pigments
- dissolved
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 239000000126 substance Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 51
- 239000000178 monomer Substances 0.000 abstract description 10
- 238000001556 precipitation Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 230000035945 sensitivity Effects 0.000 abstract description 5
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052782 aluminium Inorganic materials 0.000 abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000011521 glass Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 230000005684 electric field Effects 0.000 abstract 1
- 230000001771 impaired effect Effects 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 32
- 108091008695 photoreceptors Proteins 0.000 description 19
- 239000010410 layer Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- -1 opened Substances 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229920002382 photo conductive polymer Polymers 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 2
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910000967 As alloy Inorganic materials 0.000 description 1
- OCZBEHHGLGWOES-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C(C=C1)OC(=CC1=CC=CC=C1)C Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C(C=C1)OC(=CC1=CC=CC=C1)C OCZBEHHGLGWOES-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910001215 Te alloy Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical class C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- JLATXDOZXBEBJX-UHFFFAOYSA-N cadmium(2+);selenium(2-);sulfide Chemical compound [S-2].[Se-2].[Cd+2].[Cd+2] JLATXDOZXBEBJX-UHFFFAOYSA-N 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052981 lead sulfide Inorganic materials 0.000 description 1
- 229940056932 lead sulfide Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000002366 time-of-flight method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は光導電性高分子化合物に関し、更に詳しくは電
子写真感光体や電界発光素子等の主ャリャー輸送物質に
適する光導電性高分子化合物に関（Ｋ４）ｎ４
する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a photoconductive polymer compound, and more specifically to a photoconductive polymer compound suitable as a main carrier transport material for electrophotographic photoreceptors, electroluminescent devices, etc. Concerning (K4) n4.
［従来の技術］
従来光導電性化合物としては種々の化合物が用いられて
おり、例えば電子写真感光体においては、無機光導電性
化合物を主成分とする無ｍ感光体が、広く用いられてき
た。しかし、これらは感度、熱安定性、耐湿性、耐久性
等において必ずしも満足し得るものではない。[Prior Art] Conventionally, various compounds have been used as photoconductive compounds. For example, in electrophotographic photoreceptors, non-molecular photoreceptors containing inorganic photoconductive compounds as a main component have been widely used. . However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc.
無！！［感光体の持つ欠点を克服する目的で様々な有機
光導電性化合物を主成分とする有機感光体の研究・開発
が近年盛んに行われている。Nothing! ! [In order to overcome the drawbacks of photoreceptors, research and development of organic photoreceptors containing various organic photoconductive compounds as main components has been actively conducted in recent years.
このような有機感光体は、焼却が可能であり、無公害の
利点を有し、更に多くのものは塗工により１１形成が可
能で大量生産が容易である。それ故にコストが大幅に低
下でき、又、用途に応じて様々な形状に加工する事がで
きるという長所を有している。しかしながら、有機感光
体においては、その感度、耐久性に問題が残されており
、高感度、高耐久性の有ｉ感光体の出現が強く望まれて
いる。Such organic photoreceptors can be incinerated and have the advantage of being non-polluting, and many of them can be formed by coating, making mass production easy. Therefore, it has the advantage of being able to significantly reduce costs and being able to be processed into various shapes depending on the application. However, organic photoreceptors still have problems with their sensitivity and durability, and there is a strong desire for an organic photoreceptor with high sensitivity and high durability.
このような点を改良するため、キャリア発生機能とキャ
リア輸送機能とを異なる物質にそれぞれ分担させ、より
高性能の有機感光体を開発する試みがなされている。こ
のようないわゆる機能分館型の感光体の形態としては単
層型と積層型の２種類があり、両者ともそれぞれの材料
を広い範囲から選択することができ、任意の性能を有す
る感光体を比較的容易に作成し得ることから多くの研究
がなされてきた。このような機能分離型感光体において
、キャリヤー輸送層に用いられるキャリヤー輸送物質と
しては、キャリヤー発生層からの電荷の注入効率が大き
く、更にキャリヤー輸送層内で電荷の移動度が大である
化合物を選定する必要がある。そのためには、イオン化
ポテンシャルが小さい化合物、ラジカルカチオンが発生
しやすい化合物が選ばれるが、中でもトリアリールアミ
ン銹導体（特開昭５３−４１２６０号公報）、ヒドラゾ
ン誘導体（特開昭５７−１０１８４４号公報）、オキサ
ジアゾール誘導体（特公昭３４−５４６６号公報）、ピ
ラゾリン誘導体く特公昭５２−４１８８号公報）、スチ
ルベン銹導体（特開昭５８−１９８０４３号公報）、ト
リフェニルメタン誘導体く特公昭４５−５５５号公報〉
等の低分子化合物が従来よく用いられている。In order to improve these points, attempts have been made to develop organic photoreceptors with higher performance by assigning the carrier generation function and the carrier transport function to different substances. There are two types of photoconductors of this so-called functional library type: single-layer type and laminated type.For both, materials can be selected from a wide range, and photoconductors with arbitrary performance can be compared. A lot of research has been done on it because it is easy to create. In such a functionally separated photoreceptor, the carrier transport material used in the carrier transport layer is a compound that has high charge injection efficiency from the carrier generation layer and also has high charge mobility within the carrier transport layer. It is necessary to select. For this purpose, compounds with low ionization potential and compounds that easily generate radical cations are selected, among which are triarylamine rust conductors (Japanese Patent Laid-Open No. 53-41260) and hydrazone derivatives (Japanese Patent Laid-Open No. 57-101844). ), oxadiazole derivatives (Japanese Patent Publication No. 34-5466), pyrazoline derivatives (Japanese Patent Publication No. 52-4188), stilbene rust conductors (Japanese Patent Publication No. 58-198043), triphenylmethane derivatives (Japanese Patent Publication No. 1980-45) -555 Publication>
Low-molecular-weight compounds such as are commonly used in the past.
このようなキャリヤー輸送層は多くの場合、ポリカーボ
ネート、ポリエステル等の高分子フィルム形成性バイン
ダー中に分散または溶解された前記の如き低分子化合物
を含む。一般に、輸送層内の高分子フィルム形成性バイ
ンダーはそれ自体電気的に不活性であり、キャリヤー輸
送物質を含有したときに電気的に活性となる。Such carrier transport layers often include such low molecular weight compounds dispersed or dissolved in a polymeric film-forming binder such as polycarbonate, polyester, or the like. Generally, the polymeric film-forming binder in the transport layer is itself electrically inactive and becomes electrically active when it contains a carrier transport material.
［発明が解決しようとする課題１
しかしながら、上記の如き低分子化合物の添加はポリマ
ー系のガラス転移温度を著しく低下させ、種々の電子写
真プロセスにおける感光層の傷や感光体自体の変形等機
械的強度低下の原因となるのみならず、電荷輸送性能の
向上を目的として低分子化合物の添加堡増大をはかった
場合、該低分子化合物のポリマー中での結晶化による析
出、相分離等を引きおこし、この結果、更に感光体の機
械的強度や感度が低下する等の問題を有していた。[Problem to be Solved by the Invention 1] However, the addition of the above-mentioned low-molecular-weight compounds significantly lowers the glass transition temperature of the polymer system, resulting in mechanical problems such as scratches on the photosensitive layer and deformation of the photoreceptor itself in various electrophotographic processes. Not only will this cause a decrease in strength, but if the addition of low-molecular compounds is increased for the purpose of improving charge transport performance, the low-molecular compounds will crystallize in the polymer, causing precipitation, phase separation, etc. As a result, there were further problems such as a decrease in the mechanical strength and sensitivity of the photoreceptor.
従って本発明の目的は、結晶析出や相分離をひきおこす
ことなく、優れた機械的強度及び光導電性を感光体等に
付与しうる光導電性高分子化合物を提供することにある
。Therefore, an object of the present invention is to provide a photoconductive polymer compound that can impart excellent mechanical strength and photoconductivity to photoreceptors and the like without causing crystal precipitation or phase separation.
［課題を解決するための手段］
本発明者等は前記課題に鑑みて、鋭意研究の結果、本発
明の上記目的は、下記構造単位（■）。[Means for Solving the Problems] In view of the above-mentioned problems, the inventors of the present invention have conducted extensive research and found that the above-mentioned object of the present invention is to provide the following structural unit (■).
（ｎ）及び（ＩＩＩ）の少なくとも１つを含む繰り返し
単位を少なくとも１種有する高分子化合物を提供するこ
とにより連成されることを見出した。It has been found that coupling can be achieved by providing a polymer compound having at least one type of repeating unit containing at least one of (n) and (III).
（Ｉ）
Ｈ２
（Ｒ４）ｎイ
（ＩＩＩ）
［式中、Ｒ＋ 、Ｒ２、Ｒ３、Ｒ４及びＲ５Ｇま各々ア
ルキル基又はアルコキシ基を表わし、ｎｌ及びｎ３は各
々１〜５の整数を、ｎ２ 、ｎ４及びｎ５は各々１〜４
の整数を表わす。また、ｌ、ＩＩｌ及びｐはそれぞれ０
より大きく、１以下の数を表わす。］
以下に本発明を更に詳細に説明する。(I) H2 (R4)n (III) [In the formula, R+, R2, R3, R4 and R5G each represent an alkyl group or an alkoxy group, nl and n3 each represent an integer of 1 to 5, n2, n4 and n5 are each 1 to 4
represents an integer. Also, l, IIl and p are each 0
Represents a number greater than or equal to 1. ] The present invention will be explained in more detail below.
本発明の高分子化合物は、上記構造単位＜Ｉ＞（Ｕ）及
び（ＩＩＩ）の少なくとも１つを含む繰り返し単位を少
なくとも１種有してなるものであり、単一の繰り返し単
位からなるホモポリ、マーも、上記構造単位（Ｉ）〜（
Ｉ［［＞の少なくとも１つを含み、かつお互いに異なる
二種以上の繰り返し単位からなる共重合体も好ましく本
発明に包含されうる。更に、これらの繰返し単位と伯の
重合可能なモノマーとの共重合体も含まれる。これらは
二次元的あるいは三次元網目構造を有するものも含む。The polymer compound of the present invention has at least one type of repeating unit containing at least one of the above structural units <I> (U) and (III), and includes a homopolymer consisting of a single repeating unit, The above structural units (I) to (
Copolymers containing at least one of I[[> and consisting of two or more different repeating units may also be preferably included in the present invention. Furthermore, copolymers of these repeating units and the above polymerizable monomers are also included. These also include those having a two-dimensional or three-dimensional network structure.
本発明の高分子化合物としては、構造単位（ＩＴ）を含
むものが好ましく用いられる。As the polymer compound of the present invention, one containing a structural unit (IT) is preferably used.
本発明の高分子化合物中には上記構造単位（Ｉ）〜（Ｄ
Ｉ）の少なくとも一つが５０〜１００モル％含まれるこ
とが好ましい。In the polymer compound of the present invention, the above structural units (I) to (D
It is preferable that at least one of I) is contained in an amount of 50 to 100 mol%.
また、本発明の高分子化合物は分子量として、数平均分
子量で３．０００〜３．０００．０００、更に１０，０
００〜１００００００であることが好ましい。In addition, the polymer compound of the present invention has a number average molecular weight of 3.000 to 3.000.000, and further 10.0 to 3.000.000.
It is preferable that it is 00-1000000.
本発明において前記構造単位（Ｉ）〜（ＩＩ［）の各々
において、Ｎ原子に結合する三つのフェニル基はいずれ
も置換基Ｒ１〜Ｒ５のいずれかを有することができる。In the present invention, in each of the structural units (I) to (II[), all three phenyl groups bonded to the N atom can have any one of substituents R1 to R5.
このような置換基としてはメチル基等のアルキル基、メ
トキシ基等のアルコキシ基が挙げられる。また、０１個
のＲ１、ｎ２個のＲ２、ｎ３個のＲ３、ｎ４個のＲ４及
び０５個のＲ５はそれぞれ同一でも異なっていてもよい
。Examples of such substituents include alkyl groups such as methyl, and alkoxy groups such as methoxy. Further, 01 R1, n2 R2, n3 R3, n4 R4, and 05 R5 may be the same or different.
本発明の高分子化合物は更に前述の如く他の重合可能な
モノマーとの共重合体も含むが、このような重合可能な
モノマーとしては、例えばメタクリル酸メチル、メタク
リル酸エチル、メタクリル酸ブチル等のメタクリル酸エ
ステルモノマー、アクリル酸メチル、アクリル酸ブチル
等のアクリル酸エステルモノマー、スチレン系モノマー
、アクリロニトリル等が挙げられる。The polymer compound of the present invention further includes copolymers with other polymerizable monomers as described above, and examples of such polymerizable monomers include methyl methacrylate, ethyl methacrylate, butyl methacrylate, etc. Examples include methacrylic acid ester monomers, acrylic acid ester monomers such as methyl acrylate and butyl acrylate, styrene monomers, acrylonitrile, and the like.
本発明の高分子化合物としては、構造単位（Ｉ）とメタ
クリル酸メチルを好ましくは１：１の割合で含有するも
のが好ましく用いられる。As the polymer compound of the present invention, one containing structural unit (I) and methyl methacrylate in a ratio of preferably 1:1 is preferably used.
以下に本発明の高分子化合物の具体例を例示する。Specific examples of the polymer compound of the present invention are illustrated below.
以下余白二； ＣＨ２ ○ Ｈｓ 以下余白 以下余白 ＣＨ。Two blank spaces below; CH2 ○ Hs Margin below Margin below CH.
（分子量： ５００００〜１５００００）以下余白
以下に上記本発明の高分子化合物の合成例を挙げろが、
他の本発明の高分子化合物もこれら合成例に準じて合成
することができる。(Molecular weight: 50,000 to 150,000) Synthesis examples of the above-mentioned polymer compounds of the present invention are listed below in the margins, but other polymer compounds of the present invention can also be synthesized according to these synthesis examples.
合成例１℃本発明の高分子化合物（Ｉ１）の合成
４−ヒドロキシトリフェニルアミン２Ｑ （７，７ミ
リモル）を１００ｄ４つロフラスコに入れ、脱水したＤ
Ｍ Ｆ ４０．１２を加え溶解させた。水素化ナトリ
ウム０．３７０（７，７ミリモル）を加え固形物がなく
なるまで撹拌した。反応容器を水浴上に移し５℃まで冷
却し、クロロメチルスチレン １．ｉａｇ（７，７ミリ
モル）を滴下した。５℃で２時間反応させた後、室温で
一晩反応させた。反応液を２００ｄのイオン交換水中に
注ぎトルエンで抽出した。トルエン溶液は、イオン交換
水で水層が中性になるまで洗浄した。減圧下でトルエン
を除去し得られた赤褐色オイル状物質をトルエン／ヘキ
サン＝２／１混合溶媒に溶解させシリカゲルを用いて精
製した。Synthesis Example 1°C Synthesis of the polymer compound (I1) of the present invention Four 100 d 4-hydroxytriphenylamine 2Q (7.7 mmol) were placed in a flask, and the dehydrated D
MF 40.12 was added and dissolved. 0.370 (7.7 mmol) of sodium hydride was added and stirred until no solid matter remained. Transfer the reaction container onto a water bath, cool it to 5°C, and add chloromethylstyrene 1. iag (7.7 mmol) was added dropwise. After reacting at 5° C. for 2 hours, the reaction was continued at room temperature overnight. The reaction solution was poured into 200 d of ion exchange water and extracted with toluene. The toluene solution was washed with ion-exchanged water until the aqueous layer became neutral. Toluene was removed under reduced pressure, and the resulting reddish brown oily substance was dissolved in a 2/1 mixed solvent of toluene/hexane and purified using silica gel.
溶媒を除去して黄色オイル状物質を得た。く収量２ｇ、
収率７０％）
メチルスチリル４− （Ｎ、Ｎ−ジフェニルアミノ）−
フェニルエーテル１１．７２Ｎ Ｏ，０３１モル）、メ
タクリル酸メチル３．１１ｇ（０，０３１モルク、Ａ■
ＢＮ ｏ、３ｉｇ（０，００１９モル〉を重合用アン
プルに入れトルエンで５０１ｆｉとした後、脱気し、封
管した。Removal of the solvent gave a yellow oil. Yield 2g,
70% yield) Methylstyryl 4- (N,N-diphenylamino)-
phenyl ether 11.72N O, 031 mol), methyl methacrylate 3.11 g (0,031 mol, A
BN o, 3ig (0,0019 mol) was placed in a polymerization ampoule, adjusted to 501fi with toluene, degassed, and sealed.
重合温度６０℃、反応時間２時間で重合した。重合終了
後、直ちに冷水中でアンプルを冷やし、開封してクロロ
ホルムを加え、２０＠ ｌのメタノール中に滴下した。Polymerization was carried out at a polymerization temperature of 60° C. and a reaction time of 2 hours. Immediately after the polymerization was completed, the ampoule was cooled in cold water, opened, chloroform was added, and the mixture was dropped into 20@1 methanol.
再沈澱を２度行って目的物を得た。The target product was obtained by performing reprecipitation twice.
（乾燥重量３．１ｇ、収率２０．９％）得られたポリマ
ー中におけるトリフェニルアミンの割合は７５重」％で
あった。また、分子量は１Ｘ１０５であった。(Dry weight: 3.1 g, yield: 20.9%) The proportion of triphenylamine in the obtained polymer was 75% by weight. Moreover, the molecular weight was 1×105.
合成例２℃本発明の高分子化合物（３−１）の合成
４．４′−ジヒドロキシトリフェニルアミン１０（Ｊ
（０，０３６モ／Ｌ、）をＤ Ｍ Ｓ ０３００ｉｃ
ｌに溶解し、水素化ナトリウム（５０％ミリモル） １
９ｇを添加し、撹拌した。反応容器を５℃まで冷却し、
クロロメチルスチレン１１．９５ｇ（０，０７９モル）
を滴下した。５℃で２時間反応させた後、室温で一晩反
応させた。反応液を２００１ｐのイオン交換水中に注ぎ
、オイル分をトルエンで抽出した。トルエンを除去して
得られた赤褐色オイル成分をトルエン／ヘキサン−２フ
１溶媒を用いて精製し、目的上ツマ−を得た。（収量１
２．８！ｊ 、収率７０％）ビス（（メチルスチリル）
４−（Ｎ、Ｎ−ジフェニルアミン））フェニルエーテル
１０ｉ；ｌ （０，０２モル） 、Ａ ｒ Ｂ Ｎ
０．２ｇ（０，００１２モル）をアンプルに入れトルエ
ンで５０ｄとした後、脱気し、封管した。Synthesis Example 2°C Synthesis of Polymer Compound (3-1) of the Invention 4. 4'-Dihydroxytriphenylamine 10 (J
(0,036mo/L,) DMS 0300ic
Sodium hydride (50% mmol) dissolved in 1
9g was added and stirred. Cool the reaction vessel to 5°C,
Chloromethylstyrene 11.95g (0,079mol)
was dripped. After reacting at 5° C. for 2 hours, the reaction was continued at room temperature overnight. The reaction solution was poured into 2001p ion-exchanged water, and the oil was extracted with toluene. The reddish-brown oil component obtained by removing toluene was purified using toluene/hexane-2F1 solvent to obtain the intended product. (Yield 1
2.8! j, yield 70%) bis((methylstyryl)
4-(N,N-diphenylamine))phenyl ether 10i;l (0.02 mol), A r B N
After putting 0.2 g (0,0012 mol) into an ampoule and adding toluene to make it 50 d, it was degassed and the tube was sealed.
合成例１と同様の方法で重合を行ない目的物を得た。（
収＠ ２．Ｏｇ、収率２０％）得られたポリマー中にお
けるトリフェニルアミンの割合はａ７．７Ｍ １％であ
り、分子量は２ Ｘ １０５であった。Polymerization was carried out in the same manner as in Synthesis Example 1 to obtain the desired product. (
Collection @ 2. (20% yield) The proportion of triphenylamine in the obtained polymer was a7.7M 1%, and the molecular weight was 2 x 105.
合成例３℃本発明の高分子化合物（５−１）の合成
４．４’ ４”−１−ジヒドロキシトリフェニルア
ミン５にｌ （０，０１７モル）を１００ｄ４つロフ
ラスコに入れ、脱水したＤ Ｍ Ｆ ４０１ｇを加え溶
解させた。Synthesis Example 3°C Synthesis of the polymer compound (5-1) of the present invention 4.4'4''-1-dihydroxytriphenylamine 5 and 100 ml (0,017 mol) were placed in four flasks and dehydrated DM. 401 g of F was added and dissolved.
水素化ナトリウム１．４７ｇ（０，０６１モル）を加え
撹拌した。反応器を５℃まで冷却し、クロロメチルスチ
レン９．３７１７（０，０６１モル）を滴下し、２時間
反応させたのち室温で一晩反応させた。1.47 g (0,061 mol) of sodium hydride was added and stirred. The reactor was cooled to 5°C, 9.3717 (0,061 mol) of chloromethylstyrene was added dropwise, and the mixture was reacted for 2 hours and then overnight at room temperature.
反応液を２００１９のイオン交換水に注ぎトルエンで抽
出した。トルエン溶液を水洗し、トルエンを除去した。The reaction solution was poured into 20019 ion exchange water and extracted with toluene. The toluene solution was washed with water to remove toluene.
オイル状物質を精製し、目的モノマーを得た。（収率６
０％）
得られたモノマー５ａ （７，８Ｘ１０−３モル）と
Ａ Ｉ Ｂ Ｎ ３．０５Ｑ（０，０１９モル）をトル
エン溶液に溶解し、一部を反応させた。得られたポリマ
ー３ｇをトルエンに溶解し、Ａ Ｉ Ｂ Ｎ ０．９２
ｏを加えて、Ａ１電極をもうけたガラス基板上にスピン
コードし、膜を形成した。この膜を加熱し、３次元ポリ
マーを得た。The oily substance was purified to obtain the target monomer. (yield 6
0%) The obtained monomer 5a (7,8×10 −3 mol) and A I B N 3.05Q (0,019 mol) were dissolved in a toluene solution, and a portion was reacted. 3 g of the obtained polymer was dissolved in toluene, and A I B N 0.92
o was added and spin-coded onto a glass substrate provided with an A1 electrode to form a film. This film was heated to obtain a three-dimensional polymer.
本発明の高分子化合物は、好ましくは電子写真感光体、
電界発光素子等におけるキャリヤー輸送物質として用い
られる。電子写真感光体としては従来公知の種々の感光
体が挙げられ、そのいずれにも適用することができる。The polymer compound of the present invention is preferably applied to an electrophotographic photoreceptor,
Used as a carrier transport material in electroluminescent devices, etc. Examples of the electrophotographic photoreceptor include various conventionally known photoreceptors, and the present invention can be applied to any of them.
すなわち、種々の無機又は有機感光体、機能分離型の単
層型又は積層型感光体のいずれにも適用可能である。特
に本発明の高分子化合物と組合わせて使用可能なキャリ
ヤー発生物質としては、例えば電磁波を吸収してフリー
キャリアを発生するものであれば、無機顔料及び有機顔
料の何れも用いることができる。That is, it is applicable to any of various inorganic or organic photoreceptors, functionally separated single-layer type or laminated type photoreceptors. In particular, as the carrier generating substance that can be used in combination with the polymer compound of the present invention, both inorganic pigments and organic pigments can be used, as long as they absorb electromagnetic waves and generate free carriers.
このようなキャリヤー発生物質（ＣＧＭ）としては以下
のものが例示される。Examples of such carrier generating substances (CGM) include the following.
（Ｉ）無定型セレン、三方晶系セレン、セレン−砒素合
金、セレン−テルル合金、硫化カドミウム、セレン化カ
ドミウム、硫セレン化カドミウム、硫化水銀、硫化鉛、
酸化亜鉛、酸化チタン無定型シリコン等の無機顔料（２
）モノアゾ顔料、ポリアゾ顔料、金属錯塩アゾ顔料、ピ
ラゾロンアゾ顔料、スチルベンアゾ及びチアゾールアゾ
顔料等のアゾ系顔料
（３）アントラキノン誘導体、アントアントロン銹導体
、ジベンズピレンキノン誘導体、ビラントロン誘導体、
ビオラントロン誘導体及びイソビオラシトロン誘導体等
の７ントラキノン系又は多環字ノン系顔料
（４）インジゴ誘導体及びチオインジゴ誘導体等のイン
ジゴイド系顔料
（５）チタニルフタロシアニン、バナジルフタロシアニ
ン等の各種金属フタロシアニン、及びα型、β型、τ型
、τ型、τ′型、η型、η′型等の無金属フタロシアニ
ン等のフタロシアニン系顔料
（６）ジフェニルメタン系顔料、トリフェニルメタン顔
料、キサンチン顔料及びアクリジン顔料等のカルボニウ
ム系顔料
（７）アジン顔料、オキサジン顔料及びチアジン顔料等
のキノンイミン系顔料
（８）シアニン顔料及びアゾメチン顔料等のメチン系顔
料
キノリン系顔料
ニトロ系顔料
ニトロソ系顔料
ベンゾキノン及びナフトキノン系顔料
ナフタルイミド系顔料
ごスベンズイミダゾール誘導体等のベリノン系顔料
（Ｉ５）フルオレノン系顔料
（Ｉ６ンスクアリリウム顔料
（Ｉ１）アズレニウム化合物
更に、好ましいアゾ化合物、多環キノン系顔料の例につ
いて示す。これら化合物の具体例については特願昭６０
−２９８０１３号明ＩＩ口等に詳細に記載されている。(I) Amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide, cadmium selenide, cadmium selenide sulfide, mercury sulfide, lead sulfide,
Inorganic pigments such as zinc oxide, titanium oxide, and amorphous silicon (2
) Azo pigments such as monoazo pigments, polyazo pigments, metal complex azo pigments, pyrazolone azo pigments, stilbene azo and thiazole azo pigments (3) anthraquinone derivatives, antoanthrone rust conductors, dibenzpyrenequinone derivatives, vilanthrone derivatives,
(4) Indigoid pigments such as indigo derivatives and thioindigo derivatives (5) Various metal phthalocyanines such as titanyl phthalocyanine and vanadyl phthalocyanine, and α-type, Phthalocyanine pigments such as β-type, τ-type, τ-type, τ′-type, η-type, η′-type metal-free phthalocyanine, etc. (6) Carbonium-based pigments such as diphenylmethane pigment, triphenylmethane pigment, xanthine pigment, and acridine pigment Pigments (7) Quinoneimine pigments such as azine pigments, oxazine pigments and thiazine pigments (8) Methine pigments such as cyanine pigments and azomethine pigments Quinoline pigments Nitro pigments Nitroso pigments Benzoquinone and naphthoquinone pigments Naphthalimide pigments berynone pigments (I5) such as benzimidazole derivatives, fluorenone pigments (I6), squarylium pigments (I1) azulenium compounds, and examples of preferred azo compounds and polycyclic quinone pigments. 60
It is described in detail in No.-298013 Mei II.
以下余白
Ｎ−１）
Ａ Ｎ”Ｎ−Ａｒ’−ＣＨ＝ＣＨＡｒ ２−Ｎ＝Ｎ
ＡＡ−Ｎ ＝Ｎ−Ａｒ’−ＣＨ＝ＣＨ−Ａｒ’−ＣＨ
＝ＣＨ−ＡｒコーＮ＝Ｎ−Ａ（Ｉ−７）
（Ｉ−８）
Ａ−Ｎ＝Ｎ Ａｒ’−Ｎ＝Ｎ−Ａｒ２−Ｎ＝Ｎ Ａ
Ａ Ｎ＝Ｎ Ａｒ’ Ｎ＝Ｎ−Ａｒ
”−Ｎ＝Ｎ−ＡｒコーＮ＝Ｎ−Ａしくは未置換の炭素環
式芳香族環基、
ＲＩ Ｒ２，Ｒ３及びＲ４＝それぞれ、電子吸引性基
又は水系原子であって、Ｒ１−Ｒ４の少なくとも１つは
シアン基等の電子吸引性基、（Ｉ −１１）
／
［但し、上記各−殺伐中、
Ａ ｒＩ Ａ Ｒ２及びＡｍ３：それぞれ、ＩＪ？若
−ＮＨＳＯ２−Ｒ８（但し、Ｒ６及びＲ７はそれぞれ、
水素原子又は置換若しくは未置換のアルキル基、Ｒ８は
置換若しくは未置換のアルキル基または置換若しくは未
置換のアリール基）、Ｙは、水素原子、ハロゲン原子、
置換若しくは未置換のアルキル基、アルコキシ基、カル
ボキシル基、スルホ基、置換若しくは未置換のカルバモ
イル基または置換若しくは未置換のスルファモイル基（
但し、ｍが２以上のときは、互いに異なる基であっても
よい。）、
Ｚは、置換若しくは未置換の炭素環式芳香族環または置
換若しくは未置換の複素環式芳香族環を構成するに必要
な原子群、
Ｒ５は、水素原子、置換若しくは未置換のアミン基、Ｉ
ｆ置換若くは未置換のカルバモイル基、カルボキシル基
またはそのエステル基、
Ａｒ４は、置換若しくは未置換のアリール基、ｎは、１
または２の整数、
Ｉは、Ｏ〜４の整数である。）］
また、次の一般式［ＩＩ］群の多環キノン顔料もＣＧＭ
として使用できる。Below margin N-1) A N"N-Ar'-CH=CHAr 2-N=N
AA-N=N-Ar'-CH=CH-Ar'-CH
=CH-Ar-N=N-A(I-7) (I-8) A-N=N Ar'-N=N-Ar2-N=NA
A N=N Ar' N=N-Ar
"-N=N-Ar, N=N-A or an unsubstituted carbocyclic aromatic ring group, RI R2, R3 and R4 = each an electron-withdrawing group or a water atom, and each of R1-R4 At least one is an electron-withdrawing group such as a cyan group, (I-11) / [However, each of the above-mentioned A rI A R2 and Am3: IJ?Waka-NHSO2-R8 (However, R6 and R7 are each
a hydrogen atom or a substituted or unsubstituted alkyl group, R8 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group), Y is a hydrogen atom, a halogen atom,
Substituted or unsubstituted alkyl group, alkoxy group, carboxyl group, sulfo group, substituted or unsubstituted carbamoyl group, or substituted or unsubstituted sulfamoyl group (
However, when m is 2 or more, they may be different groups. ), Z is an atomic group necessary to constitute a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, R5 is a hydrogen atom, a substituted or unsubstituted amine group , I
f substituted or unsubstituted carbamoyl group, carboxyl group or ester group thereof, Ar4 is a substituted or unsubstituted aryl group, n is 1
or an integer of 2, I is an integer of 0 to 4. )] Polycyclic quinone pigments of the following general formula [II] group are also CGM
Can be used as
一般式［１１］ ：
（但し、この−殺伐中、Ｘ′はハロゲン原子、ニトロ基
、シアノ基、アシル基又はカルボキシル基を表わし、ｐ
はＯ〜４の整数、ｑはＯ〜６の整数を表わす。）
スクアリリウム顔料については特開昭６０−２５８５５
０号公報等に記載がある。General formula [11]: (However, in this -killing, X' represents a halogen atom, a nitro group, a cyano group, an acyl group, or a carboxyl group, and p
represents an integer from O to 4, and q represents an integer from O to 6. ) For squarylium pigments, see JP-A-60-25855.
There is a description in Publication No. 0, etc.
チタニルフタロシアニンについては特願昭６２−２４１
９８３号明細書に記載がある。Regarding titanyl phthalocyanine, patent application 1986-241
It is described in the specification of No. 983.
アズレニウム化合物については、特願昭６２−２５１１
８８号明細書に記載がある。Regarding azulenium compounds, patent application No. 62-2511
It is described in the specification of No. 88.
更に、特殊な無金属フタロシアニンについて、特願昭６
１−２９５７８４号明細書等に記載がある。Furthermore, regarding a special metal-free phthalocyanine, a patent application was filed in 1983.
It is described in the specification of No. 1-295784.
し実施例］
以下に、本発明を実施例を挙げて更に具体的に説明する
。EXAMPLES] The present invention will be described in more detail below with reference to Examples.
実施例１
合成例１で合成した本発明の高分子化合物（２−１）を
用いた試料を以下のようにして作製した。Example 1 A sample using the polymer compound (2-1) of the present invention synthesized in Synthesis Example 1 was prepared as follows.
ガラス基板上に、アルミニウム電極を蒸着した。An aluminum electrode was deposited on the glass substrate.
その上にセレンを蒸着しキャリヤー発生層とした。Selenium was vapor-deposited thereon to form a carrier generation layer.
本発明の高分子化合物（２−１）０．５！ｌを１゜２−
ジクロロメタン５１１２に溶解した溶液をスピンコータ
ーを用いて約８μｍの厚みに塗布し、キャリヤー輸送層
を形成した。Polymer compound (2-1) of the present invention 0.5! l to 1゜2-
A solution dissolved in dichloromethane 5112 was applied to a thickness of about 8 μm using a spin coater to form a carrier transport layer.
さらにこの上にアルミニウム電極を蒸着し、移動度及び
耐摩耗性測定用の試料とした。Further, an aluminum electrode was vapor-deposited thereon to prepare a sample for measuring mobility and wear resistance.
移動度は通常用いられるＴＯＦ法（タイムオアフライト
法）を用いて測定した。Mobility was measured using the commonly used TOF method (time-or-flight method).
また、耐摩耗試験はテーパー型摩耗試験機を用い、摩耗
輪Ｃ３−１０、荷重５００にｌ ｆで測定した。Further, the wear resistance test was carried out using a taper type wear tester, using a worn ring C3-10, a load of 500, and lf.
更にキャリア輸送層における析出の程度を目視にて評価
した。Furthermore, the degree of precipitation in the carrier transport layer was visually evaluated.
結果を表１に示す。The results are shown in Table 1.
実施例２
合成例２で合成した本発明の高分子化合物（３１）０．
２ｇを１，２−ジクロロエタンに２ｇに溶解させた溶液
を用いてキャリヤー輸送層を形成した以外は、実施例１
と同様にして、移動度及び耐摩耗性測定用試料を作製し
、同様に評価した。Example 2 Polymer compound (31) of the present invention synthesized in Synthesis Example 2 0.
Example 1 except that the carrier transport layer was formed using a solution of 2 g dissolved in 1,2-dichloroethane.
Samples for mobility and wear resistance measurements were prepared in the same manner as above, and evaluated in the same manner.
結果を表１に示す。The results are shown in Table 1.
実施例３
合成例３で合成した本発明の高分子化合物（５−１）を
用いてキャリヤー輸送層を形成し、試料の上部にＳｅを
蒸着し、その上にＡｒを蒸着してキャリヤー発生層とし
た以外は実施例１と同様にして移動度及び耐摩耗性測定
用試料を作成し、同様に評価した。結果を表１に示す。Example 3 A carrier transport layer was formed using the polymer compound (5-1) of the present invention synthesized in Synthesis Example 3, Se was evaporated on the top of the sample, and Ar was evaporated thereon to form a carrier generation layer. Samples for measuring mobility and abrasion resistance were prepared in the same manner as in Example 1 except that the samples were evaluated in the same manner. The results are shown in Table 1.
比較例１
トリフェニルアミン０．５ｇ、ダイヤナールＢＲ−８０
１１（三菱レイヨン社製、アクリル樹脂）を１．２−ジ
クロロエタン１０戴に溶解させた溶液をキャリヤー輸送
層形成用塗布液として用い、キャリヤー輸送層を形成し
た以外は、実施例１と同様の方法で移動度及び耐摩耗性
測定用試料を作製し、同様に評価した。結果を表１に示
す。Comparative Example 1 Triphenylamine 0.5g, Dianaru BR-80
The method was the same as in Example 1, except that a solution of 11 (manufactured by Mitsubishi Rayon Co., Ltd., acrylic resin) dissolved in 1,2-dichloroethane 10 was used as the coating solution for forming the carrier transport layer, and the carrier transport layer was formed. A sample for measuring mobility and wear resistance was prepared using the same method and evaluated in the same manner. The results are shown in Table 1.
比較例２
ポリビニルカルバゾール（阿南香料社製ツビコール２１
００．２ ｉＪを１，２−ジクロロエタン５１Ｑに溶解
させた溶液をキャリヤー輸送層形成用塗布液として用い
、キャリヤー輸送層を形成した以外は実施例１と同様に
して移動度及び耐摩耗性測定用試料を作製し、同様に評
価した。結果を表１に示す。Comparative Example 2 Polyvinylcarbazole (Tubicol 21 manufactured by Anan Fragrance Co., Ltd.)
A solution prepared by dissolving 00.2 iJ in 1,2-dichloroethane 51Q was used as a coating solution for forming a carrier transport layer, and the same procedure as in Example 1 was carried out except that the carrier transport layer was formed for mobility and abrasion resistance measurement. Samples were prepared and evaluated in the same manner. The results are shown in Table 1.
実施例４
本発明の高分子化合物（Ｉ−１）として分子量が２ｘｉ
ｏ”ｔのものを用いた以外は実施例１と同様にして移動
度及び耐摩耗性測定用試料を作製し、同様に評価した。Example 4 The polymer compound (I-1) of the present invention has a molecular weight of 2xi
Samples for measuring mobility and abrasion resistance were prepared in the same manner as in Example 1, except that a sample of o"t was used, and evaluated in the same manner.
結果を表１に示す。The results are shown in Table 1.
実施例５
本発明の高分子化合物（Ｉ−１）として分子ｍが５ Ｘ
１０８のものを用いた以外は実施例１と同様にして移
動度及び耐摩耗性測定用試料を作製し、同様に評価した
。結果を表１に示す。Example 5 The polymer compound (I-1) of the present invention has a molecule m of 5
Samples for measuring mobility and abrasion resistance were prepared in the same manner as in Example 1, except that No. 108 was used, and evaluated in the same manner. The results are shown in Table 1.
以下余白
表−１
［発明の効果］
以上詳細に述べたように、本発明の高分子化合物により
、結晶析出ヤ相分離をひきおこすことなく、優れた機械
的強度及び光導電性を感光体等に付与することができる
。Table 1 below: [Effects of the Invention] As described in detail above, the polymer compound of the present invention provides excellent mechanical strength and photoconductivity to photoreceptors, etc., without causing crystal precipitation or phase separation. can be granted.
＊１移動度：膜厚８μｍ、電圧３００Ｖで行なった。*1 Mobility: Conducted at a film thickness of 8 μm and a voltage of 300V.
＊２析 出二 〇：析出なし
×：析出有
表１より明らかなように、本発明の高分子化合物を使用
した実施例１〜５はいずれも本発明外のキャリヤー輸送
物質を用いた比較例１及び２のいずれに対しても優れた
移動度、耐摩耗性及び析出性を有している。*2 Precipitation 2 〇: No precipitation ×: Precipitation present As is clear from Table 1, Examples 1 to 5 using the polymer compound of the present invention are all comparative examples using a carrier transport material other than the present invention. It has excellent mobility, wear resistance, and precipitation properties compared to both No. 1 and No. 2.
特許出願人 口二カ株式会社（他１名）代 理 人 弁
理士 市之瀬 宮夫Patent applicant Kuchinika Co., Ltd. (and one other person) Representative Patent attorney Miyao Ichinose
Claims (1)
１つを含む繰り返し単位を少なくとも１種有する高分子
化合物。 （ I ）▲数式、化学式、表等があります▼ （II）▲数式、化学式、表等があります▼ （III）▲数式、化学式、表等があります▼ ［式中、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４及びＲ＿５は
各々アルキル基又はアルコキシ基を表わし、ｎ＿１及び
ｎ＿３は各々１〜５の整数を、ｎ＿２、ｎ＿４及びｎ＿
５は各々１〜４の整数を表わす。また、ｌ、ｍ及びｐは
それぞれ０より大きく、１以下の数を表わす。］[Scope of Claims] A polymer compound having at least one repeating unit containing at least one of the following structural units (I), (II) and (III). (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1, R_2, R_3, R_4 and R_5 each represent an alkyl group or an alkoxy group, n_1 and n_3 each represent an integer of 1 to 5, n_2, n_4 and n_
5 each represents an integer from 1 to 4. Further, l, m, and p each represent a number greater than 0 and less than or equal to 1. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2254723A JP2546739B2 (en) | 1990-09-25 | 1990-09-25 | Photoconductive polymer compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2254723A JP2546739B2 (en) | 1990-09-25 | 1990-09-25 | Photoconductive polymer compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04133065A true JPH04133065A (en) | 1992-05-07 |
| JP2546739B2 JP2546739B2 (en) | 1996-10-23 |
Family
ID=17268955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2254723A Expired - Fee Related JP2546739B2 (en) | 1990-09-25 | 1990-09-25 | Photoconductive polymer compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2546739B2 (en) |
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